Re: PPTP vs. SSL

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Author: jordi laforge
Date:  
To: Main PLUG discussion list
Subject: Re: PPTP vs. SSL
Ah ha! THanks!

On 10/22/06, George Toft <> wrote:
>
> In a word - no.
>
> Let's assume you are sending a packet with some text via some
> application. It gets encrypted, and header/trailer info is added. It
> might even get fragmented based on MTU size. At the other end, the
> packets get reassembled, unencrypted, and presented to the application.
> Since the payload (or data) is encrypted at a higher layer, that
> payload remains encrypted in the lower layers.
>
> The reverse is true as well on the other end - once the packets are
> reassembled and decrypted, the payload can be read normally. This is
> why the VPN endpoint needs to be controlled - once the data is out of
> the tunnel, it's fair game to sniff and record.
>
> George Toft, CISSP, MSIS
> 623-203-1760
>
>
>
>
> jordi laforge wrote:
> > Thanks for the information. While I am new to VPNs I do understand the
> > concept of how they work. That said I do appreciate all the good info
> > you gave and will read those links.
> >
> > In order to save an email I'd like to include a question I had from one
> > of Eric's emails.
> > Since SSL vpns work at a higher OSI layer does that mean that the stuff
> > at the lower layers is not encrypted? Like mac address and ip address.
> > THanks all for answering my questions. You are most helpfull.
> >
> >
> > On 10/21/06, *Kurt Granroth* <
> > <mailto:plug-discuss@granroth.org>> wrote:
> >
> >     jordi laforge wrote:
> >      > I'm trying to provide a roadwarrior situation. Here is what I'm
> >     looking at:
> >      > Small 8-12 user lan.
> >      > 4-5 of these users have home pc's(Windows) that they'd like to
> use to
> >      > connect to the
> >      > office and user the file server\ email\ databases.
> >      > The windows file server has PPTP capabilities.
> >      >
> >      > I could either use the Windows PPTP or setup another server
> running
> >      > Linux with openvpn. Or something else I haven't thought of....but
> >     you
> >      > guys suggest.
> >      > Whaddya think?

> >
> >     Okay, it sounds like you're not all that familiar with VPNs in
> general,
> >     based on your comments here and in later messages.  I *strongly*
> suggest
> >     doing some quick reading on that topic first before getting into
> >     specifics.  The 'howstuffworks' entry on VPNs is not half-bad and
> the
> >     wikipedia page is excellent.

> >
> >     Here's the very very short summary: A VPN would allow your 'road
> >     warriors' to connect to the home office while they are at home or on
> >     the
> >     road.  The user's remote laptop or desktop would get a special IP
> that
> >     is specific to the VPN through which all traffic to work is
> 'tunneled'
> >     in an encrypted manner.  Done properly, the remote worker would be
> able
> >     to access ALL of the services that she could normally access while
> in
> >     the office... but in a safe and secure manner over the public
> Internet.

> >
> >     Now PPTP has the advantage here of being very easy to setup and if
> you
> >     have one of the Windows Servers, then you have half of it already
> nearly
> >     setup.  You would need to get clients for any Linux users, but
> that's
> >     not a problem as I'm fairly certain that there is now "native"
> support
> >     in the kernel.

> >
> >     HOWEVER, PPTP is considered to be fundamentally broken by some
> respected
> >     cryptographers.  A quote from Bruce Schneier: "Microsoft PPTP is
> very
> >     broken, and there's no real way to fix it without taking the whole
> >     thing
> >     down and starting over."

> >
> >     http://www.schneier.com/pptp-faq.html

> >
> >     OpenVPN is a free solution that has so far been proven to be
> rock-solid.
> >     It is, however, not as easy to setup as PPTP.  In fact, if you want
> to
> >     do anything more than a peer-to-peer setup, you will likely have to
> do a
> >     considerable bit of reading and some configuration file editing.

> >
> >     Mind you, while the reading is verbose, it's not hard to understand
> and
> >     it shouldn't take more than a few hours to get everything
> setup.  I'm
> >     told, too, that some of the GUIs available make it a lot easier
> (haven't
> >     used any of them) and some of the specialized distros like
> Smoothwall
> >     and IPCop should make it even easier yet.

> >
> >     Now this is a Linux group so we'll tend to lean towards using Linux
> >     based solution for the "server" side.  I'm honor bound to tell you,
> >     though, that you don't have to.  OpenVPN is fundamentally a
> >     peer-to-peer
> >     VPN (with some variances) and works just dandy on Windows.  So you
> >     *could* run it as a service on your Windows Server and it would
> likely
> >     chug away just fine.  There is even a handy GUI for it.

> >
> >     I recommend starting with some reading:

> >
> >     http://openvpn.net/howto.html
> >     http://openvpn.net/INSTALL-win32.html
> >     http://openvpn.se/ <http://openvpn.se/>
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